Judge Ronald J.H. O’Leary was appointed to Cleveland Housing Court by Ohio Governor John Kasich in March 2017 to fill the seat of Judge Raymond Pianka who passed away in January 2017. Judge O’Leary attended Miami University where he obtained a bachelor’s degree in Diplomacy and Foreign Affairs and a master’s degree in Political Science. He then moved to Cleveland to attend law school at Case Western Reserve University and started his legal career at the City of Cleveland’s Prosecutor’s Office in 1998.

From 1999 to 2005, Judge O'Leary was the Chief Assistant Director of Law for Code Enforcement in the Cleveland Law Department. The Code-Enforcement attorneys brought criminal and civil cases on Cleveland's behalf in Housing Court. In 2006, Mayor Frank Jackson appointed Judge O'Leary to be the Assistant Director of the Cleveland Department of Building and Housing. In 2014, Mayor Jackson appointed Judge O'Leary as Director of the Building and Housing Department. He held that position until his appointment to Housing Court.